cyclohexyl 2-azido-4-benzylamino-4-N-3-O-carbonyl-2,4,6-trideoxy-α-D-galactopyranoside | 1258284-52-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: cyclohexyl 2-azido-4-benzylamino-4-N-3-O-carbonyl-2,4,6-trideoxy-α-D-galactopyranoside
• 英文别名: (3aS,4R,6S,7R,7aS)-7-azido-3-benzyl-6-cyclohexyloxy-4-methyl-4,6,7,7a-tetrahydro-3aH-pyrano[3,4-d][1,3]oxazol-2-one
• CAS: 1258284-52-4
• 化学式: C₂₀H₂₆N₄O₄
• 分子量: 386.451
• InChiKey: OTGFVHZKKMOYRO-LQDZTQBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  62.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-azido-4-benzylamino-4-N-3-O-carbonyl-2,4,6-trideoxy-D-galactopyranosyl trichloroacetimidate 、 环己醇 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 生成 cyclohexyl 2-azido-4-benzylamino-4-N-3-O-carbonyl-2,4,6-trideoxy-β-D-galactopyranoside 、 cyclohexyl 2-azido-4-benzylamino-4-N-3-O-carbonyl-2,4,6-trideoxy-α-D-galactopyranoside
  参考文献：
  名称：

  A novel glycosyl donor for synthesis of 2-acetamido-4-amino-2,4,6-trideoxy-α-d-galactopyranosides

  摘要：

  2-Azido-4-benzylamino-4-N-,3-O-carbony1-2,4,6-trideoxy-D-galactopyranosyl trichloroacetimidate (14) was conveniently prepared in six steps by regioselective introduction of an N-benzyl carbamate at O-3 of 6-deoxy-D-glucal 6, followed by mesylation at O-4. Intramolecular displacement of the leaving group afforded oxazolidinone 11. Azidonitration of the bicyclic glycal 11 gave the glycosyl nitrate anomers 12 in good yield and stereoselectivity. Hydrolysis of the anomeric nitrates under aqueous conditions gave the pyranose 13, which was easily converted into the imidate 14. Glycosylation of cyclohexanol by 14 gave glycosides 16 alpha and 16 beta in a ratio of 4:1. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.08.017